Sodium Thiosulfate → 3-(2-Benzyloxy-ethoxymethyl)-4-(4-chloro-benzenesulfonyl)-5,8-difluoro-chroman

HRID 564316Notes

Reaction equation

HRID 564316 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH:13]1[CH:22](SC2C=CC(Cl)=CC=2)[C:21]2[C:16](=[C:17]([F:32])[CH:18]=[CH:19][C:20]=2[F:31])[O:15][CH2:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:33]1[CH:38]=[C:37]([Cl:39])[CH:36]=[C:35](C(OO)=O)[CH:34]=1.[S:44]([O-:48])([O-])(=[O:46])=S.[Na+].[Na+]>C(Cl)Cl.O.C(OCC)(=O)C>[CH2:1]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH:13]1[CH:22]([S:44]([C:34]2[CH:33]=[CH:38][C:37]([Cl:39])=[CH:36][CH:35]=2)(=[O:48])=[O:46])[C:21]2[C:16](=[C:17]([F:32])[CH:18]=[CH:19][C:20]=2[F:31])[O:15][CH2:14]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 670064253-(2-Benzyloxy-ethoxymethyl)-4-(4-chloro-phenylsulfanyl)-5,8-difluoro-chroman

Product 1

HCID 670069033-(2-Benzyloxy-ethoxymethyl)-4-(4-chloro-benzenesulfonyl)-5,8-difluoro-chroman

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(2-Benzyloxy-ethoxymethyl)-4-(4-chloro-phenylsulfanyl)-5,8-difluoro-chroman (0.42 g, 0.88 mmole) was dissolved in 15 ml DCM and MCPBA (77%, 0.6 g, 2.6 mmole) was added. The reaction was stirred at room temperature for 30 minutes. 0.5 g sodium thiosulfate in 50 ml water and 50 ml EtOAc were added. The organic layer washed with 1N NaOH solution (50 ml), brine (50 ml), dried over sodium sulfate and concentrated. The product was purified by column (EtOAc/hexane from 0/100 to 50/50 in 45 minutes). Yield: 0.40 g, 89%. 1H NMR (CDCl3 400 MHz δ 7.73 (d, J=8.8 Hz, 2H), 7.4 (d, J=8.1 Hz, 2H), 7.25-7.37 (m, 5H), 7.02 (m, 1H), 6.42 (m, 1H), 4.90 (dd, J=11.7 and 2.9 Hz, 1H), 4.63 (s, 1H), 4.50 (s, 2H), 4.38 (t, J=11.0, 1H), 3.45-3.62 (m, 5H), 3.30 (t, J=9.5 Hz, 1H), 3.13 (m, 1H).

Workup

  1. washThe organic layer washed with 1N NaOH solution (50 ml), brine (50 ml)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe product was purified by column (EtOAc/hexane from 0/100 to 50/50 in 45 minutes)

Sources & evidence

ORD record
ord-5c840a32b7074569800b9335517e7f56
Source dataset
uspto-grants-2011_11
Patent number
US08067621B2

Reaction notes

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